The Wellfellow Guide to Bottoming

August 13, 2017

8 minute read

“When a hung top is hosting but you can’t go because you just ate fifteen tacos by yourself,” reads a hilarious meme from the popular Instagram account, best_of_grindr. This message is posted above a photo of a crying Zac Efron. There’s no doubt it’s funny, for a multitude of reasons, but it also indicates a bit of common knowledge about being a bottom. Is it true that a delightful, authentic Mexican meal makes for messy anal sex?

Whenever we see gay sex portrayed in mainstream programming, it’s often sweet, sensual, and candlelit—more about the connection between the characters than the sex itself. From the fantastical, groundbreaking scenes on American Gods to the PG-13 hotness of How to Get Away with Murder to the gaggle of TV teens losing their V-card on ABC Family, writers and TV producers seem to be obsessed with showing us at our most vulnerable moments. But those vulnerable moments never include how-to’s. Only gay porn seems to hint at the awkwardness of fumbling around with all our “equipment”. And, provided that America’s schools aren’t offering gay sex ed, these are the sources by which we’ve all learned about sex. None of these sources indicate what it’s truly like to get pounded by that hung top, with or without gorging on tacos al pastor.

Bottom 101

Whether you’re a newbie to gay sex, a top in search of new adventures, or a veteran bottom hoping to improve your skills, it never hurts to revisit a little gay sex 101.

We tend to think of bottoms exclusively as cisgender gay men who have anal sex. However, this also includes our transgender brothers and both their anal intercourse or frontal, vaginal sex. Additionally, bottoming isn’t restricted to just those who identify as bottoms. Versatile men, vers/bottoms, and even some tops find themselves as the receptive partner. Thus, these bottoming lessons are important for every gay man, regardless of his preferred sexual role.

Bottoms are essentially the brains of the operation. Sure, the top has the necessary tool for the job. But it’s the bottom who runs the show.

“Tops may get the glory, but bottoms make the world go round,” writes The Advocate’s Tyler Curry. “To be a good bottom, a guy has to know what works for his body, how to maintain a healthy and hygienic rear end, and how to navigate his sexual health without compromising his pleasure. Quite simply, tops have it easy when it comes to sex, because being a good bottom is no easy job.”

Being a bottom is about so much more than lying there. From the prep to the actual sexual experience, there’s a lot on your plate. Luckily, we’re here to help you figure it all out.

The Psychology Behind Bottoming

Depending on your frame of reference, you’ve likely heard some inaccurate conclusions about bottoms (i.e. all bottoms are femmes or twinks). But there’s plenty for bottoms to celebrate. A 2009 Scientific American study found that bottoms were less likely to harbor internalized homophobia and more likely to accept their gay identity. And versatile men had greater psychological health because of their vast range of sexual experience. If you’ve had a negative view of bottoming in the past, let it go. You stand to gain a lot.

Your First Time

If you’re bottoming for the first time, there’s a lot to know, so pull out your notepad and pay close attention.

Grooming: Before you worry about cleanliness below the belt, take care of some other minor details like cutting and filing your fingernails. This is an often-overlooked detail, and it might seem unrelated but it matters. You’ll probably use your own hand to finger yourself and loosen up your sphincter, or even to help slide your partner in. A jagged nail could cut you or him. Not a great way to start.

Practice Makes Perfect: Take those newly trimmed fingernails and go to work. You need to get used to the sensation. Granted, one or two fingers isn’t the same as a penis. But you’ll at least get an idea of what to expect. Lube your fingers and practice in bed or play around in the shower.

Cleaning: This is THE most important step in preparing for your first time as a bottom. Every bottom’s worst fear is having an unexpected bowel movement or discharge after sex. You can avoid this by taking great care of yourself beforehand. Eat a high fiber diet so you can keep your system cleaned out. Wash in the shower thoroughly. And then wash again. And again. If you’re not confident about cleaning with soap and water, invest in an enema or douche. While these options aren’t the most pleasant, they’re guaranteed to clean you out.

Pee First: Anal penetration stimulates the prostate, which makes you feel like you have to pee. So, make sure you go beforehand to reduce that feeling. Otherwise, you’ll need to stop just when things are getting good.

Condoms & Lube: There’s no way around it—your first time can be painful. But that pain can be significantly reduced by using condoms and lube. The easier it is for him to slide in, the more relaxed you’ll feel. You can try desensitizing lube if needed. But be careful as these lubes reduce your ability to detect unnatural pain. And of course, condoms reduce the spread of STDs.

Relax: Your body will naturally tighten up when he first enters you. But the more you clench to brace for pain, the more it’ll hurt. Relax your sphincter so he can enter without facing resistance. Take some deep breaths. Or practice controlling your sphincter with kegel exercises. And, you might feel like you need to poop, but don’t fret. You’re using a lot of the same muscles involved in a bowel movement, hence the same sensation. The more experience you have, the more you’ll be able to differentiate the feelings.

Slow Down: If your top starts pumping like his waist is attached to a boat motor, slow him down. If he takes his time in the beginning, only partially inserting with slower thrusts, you’ll start to loosen up over time. So, by the moment he fully inserts, you’ll be more relaxed and the sex will be more enjoyable.

Your Pleasure: As a bottom, you aren’t just reduced to the role of pleasure toy for your top. Remember to stroke yourself too. Your pleasure throughout this experience is just as important as his.

You Might Need More Tries: Don’t expect to be a bottoming expert during your first experience. You might feel that you can’t take a full insertion on the first try. “I take my time and I get it in about 2 or 3 inches. I’m thinking to myself, ‘Fuck, is this all I can handle?’,” writes JustUsBoys forum user 123kid about his first time bottoming. Know that things might not go as planned. Also, know that bottoming may not be for you.

Bottoming Over Time

Your first time bottoming could be a triumph or a disaster. Either way, know that it gets better over time. Not only will you be able to handle full insertion but you’ll also enjoy longer sessions. You’ll try different positions. And your fears around fecal matter and different sensations will dissipate. Like with anything, the more times you bottom, the more you’ll learn about what you enjoy and how to communicate that to your partner.

Being a better bottom

If you need some guidance on how to become a better bottom over time, there are a few places you can start.

Clean Differently: There’s more than one way to approach a pre-intercourse cleaning session. You can try a shower attachment, a douching bulb, an enema, or just a towel. Try them all but once you find the method that works for you, stick with it so you don’t have variable results.

Train Your Butt: Practice still makes perfect. Preparing yourself for anal play isn’t restricted to your first time. To get more comfortable, you should keep practicing over time. Try out butt plugs, dildos, and the wide array of other sex toys on the market. Just steer clear of those hard plastic dildos—they’re nothing like a real penis, even if they have all those veins on them.

New Positions: Once you find a comfortable position for anal, you’ll want to stick with it. You won’t want to experience any further pain. But the same position over and over can get stale for both you and your partner, especially if you’re monogamous. Be open to trying new things and don’t hold onto missionary.

Foreplay First: You might want to try rimming and foreplay before any insertion happens. It heightens the passion between you two, and it gives you time to loosen up without halting the flow.

Control: Remember, the bottom is the star of the show. Your comfort matters. Make sure you’re vocal about the speed of his thrusts and how deep he goes in. If you’re in pain or want things to be more sensual, say it out loud. Your top is a lot of things but a mind reader isn’t one of them.

Bottom Safety

One last thing. Whether you choose to play safe or bareback, you should know the facts. The lining of your anus is far more likely to rip, tear, and develop abrasions during intercourse. The presence of these tears allows HIV and other STDs to enter your bloodstream. This can happen after ejaculation and with pre-cum. Thus, it’s important to understand your risk factors, which are higher than a top’s, before making any decisions.

To protect yourself, talk to your doctor about your PrEP options and stock up on condoms. There’s even a “bottom condom”, which is really the female condom. It’s a condom with a looser fit and non-latex material that uses a ring to stay put in the rectum.

If you opt to forgo protection, make sure you have an open dialogue with your partner about his HIV status and get yourself tested on a regular basis.

Bottoming can be an enjoyable, pleasurable experience provided you do your prep work and open yourself to everything it entails. Newbies and veterans alike can continue improving their sex lives with these strategies. All it takes is practice and an open mind.